United States Patent No. 3,700,681 issued on Oct. 24, 1972 discloses and claims bronchodilators for usein mammals identified as 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-aminoethyl)pyridines. Included in this group of pyridines disclosed and claimed in U.S. Pat. No. 3,700,681 is the t-butyl form of the above-identified pyridines which is represented by the following formula: ##STR1##
The present invention relates to a process not disclosed or suggested in U.S. Pat. No. 3,700,681 for producing the t-butyl form of the subject pyridines. The present process has particular interest since it was unexpectedly found the t-butyl form of the patented pyridines can be produced with a two-step reaction sequence as opposed to the many reaction steps required in U.S. Pat. No. 3,700,681. In addition, it was determined that the present process unexpectedly produces the product in high yield and purity.
Also within the purview of the instant invention are the compounds 2-hydroxymethyl-3-benzyloxypyridine-6-epoxyethane, 2-phenyl-4H-pyrido[3,2-d]-1,3-dioxin-6-epoxyethane and 2,2-disubstituted-4H-pyrido[3,2-d]-1,3-dioxin-6-epoxyethanes. These compounds were found to be excellent intermediates in the process of the present invention.